US6562172B1 - Glass decorating method using ink compositions containing N-vinyl lactams - Google Patents
Glass decorating method using ink compositions containing N-vinyl lactams Download PDFInfo
- Publication number
- US6562172B1 US6562172B1 US09/134,825 US13482598A US6562172B1 US 6562172 B1 US6562172 B1 US 6562172B1 US 13482598 A US13482598 A US 13482598A US 6562172 B1 US6562172 B1 US 6562172B1
- Authority
- US
- United States
- Prior art keywords
- ink
- alkyl
- substrate
- vinyl lactam
- straight
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 69
- 238000000034 method Methods 0.000 title claims abstract description 39
- 229920002554 vinyl polymer Polymers 0.000 title claims abstract description 31
- 239000011521 glass Substances 0.000 title abstract description 19
- 239000000758 substrate Substances 0.000 claims abstract description 62
- 239000011888 foil Substances 0.000 claims abstract description 35
- 238000013461 design Methods 0.000 claims abstract description 22
- 230000005855 radiation Effects 0.000 claims abstract description 22
- 238000003825 pressing Methods 0.000 claims abstract description 3
- 239000000178 monomer Substances 0.000 claims description 40
- -1 glyceryl fatty ester Chemical class 0.000 claims description 38
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- 125000004432 carbon atom Chemical group C* 0.000 claims description 27
- 125000003118 aryl group Chemical group 0.000 claims description 24
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 14
- 239000002736 nonionic surfactant Substances 0.000 claims description 13
- JWYVGKFDLWWQJX-UHFFFAOYSA-N 1-ethenylazepan-2-one Chemical compound C=CN1CCCCCC1=O JWYVGKFDLWWQJX-UHFFFAOYSA-N 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 229920001223 polyethylene glycol Polymers 0.000 claims description 9
- 239000002202 Polyethylene glycol Substances 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 6
- 125000002723 alicyclic group Chemical group 0.000 claims description 6
- 125000002619 bicyclic group Chemical group 0.000 claims description 6
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims description 6
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 229910000077 silane Inorganic materials 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 5
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 4
- 239000002318 adhesion promoter Substances 0.000 claims description 4
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 150000003951 lactams Chemical class 0.000 claims description 3
- 239000000976 ink Substances 0.000 description 57
- 239000000049 pigment Substances 0.000 description 18
- 239000010410 layer Substances 0.000 description 15
- 229920001577 copolymer Polymers 0.000 description 12
- 0 [1*]C(=C)C Chemical compound [1*]C(=C)C 0.000 description 11
- 239000002253 acid Substances 0.000 description 11
- 150000004756 silanes Chemical class 0.000 description 11
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 10
- 230000001681 protective effect Effects 0.000 description 10
- 239000012952 cationic photoinitiator Substances 0.000 description 9
- 150000003254 radicals Chemical class 0.000 description 9
- 238000005034 decoration Methods 0.000 description 8
- 239000004831 Hot glue Substances 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- 239000004094 surface-active agent Substances 0.000 description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 6
- 239000002518 antifoaming agent Substances 0.000 description 6
- 150000002118 epoxides Chemical class 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- CYUZOYPRAQASLN-UHFFFAOYSA-N 3-prop-2-enoyloxypropanoic acid Chemical compound OC(=O)CCOC(=O)C=C CYUZOYPRAQASLN-UHFFFAOYSA-N 0.000 description 5
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 5
- 125000003342 alkenyl group Chemical group 0.000 description 5
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 125000002091 cationic group Chemical group 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 description 4
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical class C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 description 4
- 229920000570 polyether Polymers 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920002379 silicone rubber Polymers 0.000 description 4
- 239000004945 silicone rubber Substances 0.000 description 4
- 239000012815 thermoplastic material Substances 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000000919 ceramic Substances 0.000 description 3
- 229940096386 coconut alcohol Drugs 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- QDOXWKRWXJOMAK-UHFFFAOYSA-N dichromium trioxide Chemical compound O=[Cr]O[Cr]=O QDOXWKRWXJOMAK-UHFFFAOYSA-N 0.000 description 3
- 238000010894 electron beam technology Methods 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 3
- 229910052737 gold Inorganic materials 0.000 description 3
- 239000010931 gold Substances 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 229920000915 polyvinyl chloride Polymers 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000001054 red pigment Substances 0.000 description 3
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical class [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- MUTNCGKQJGXKEM-UHFFFAOYSA-N tamibarotene Chemical group C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1NC(=O)C1=CC=C(C(O)=O)C=C1 MUTNCGKQJGXKEM-UHFFFAOYSA-N 0.000 description 3
- 229920001169 thermoplastic Polymers 0.000 description 3
- 239000004416 thermosoftening plastic Substances 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- NQOGBCBPDVTBFM-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol;prop-2-enoic acid Chemical compound OC(=O)C=C.CC(O)COC(C)COC(C)CO NQOGBCBPDVTBFM-UHFFFAOYSA-N 0.000 description 2
- GTELLNMUWNJXMQ-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical class OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.CCC(CO)(CO)CO GTELLNMUWNJXMQ-UHFFFAOYSA-N 0.000 description 2
- FGSFVBRPCKXYDI-UHFFFAOYSA-N 2-triethoxysilylethyl 2-methylprop-2-enoate Chemical compound CCO[Si](OCC)(OCC)CCOC(=O)C(C)=C FGSFVBRPCKXYDI-UHFFFAOYSA-N 0.000 description 2
- 229910001369 Brass Inorganic materials 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- IRERQBUNZFJFGC-UHFFFAOYSA-L azure blue Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[S-]S[S-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-] IRERQBUNZFJFGC-UHFFFAOYSA-L 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 2
- 239000010951 brass Substances 0.000 description 2
- 238000010538 cationic polymerization reaction Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000009500 colour coating Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000005038 ethylene vinyl acetate Substances 0.000 description 2
- 235000001727 glucose Nutrition 0.000 description 2
- 229920000578 graft copolymer Polymers 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- 239000001023 inorganic pigment Substances 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012860 organic pigment Substances 0.000 description 2
- 150000001282 organosilanes Chemical class 0.000 description 2
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920001282 polysaccharide Polymers 0.000 description 2
- 239000005017 polysaccharide Substances 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 2
- RQGPLDBZHMVWCH-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole Chemical class C1=NC2=CC=NC2=C1 RQGPLDBZHMVWCH-UHFFFAOYSA-N 0.000 description 2
- 238000007650 screen-printing Methods 0.000 description 2
- 238000012216 screening Methods 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
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- 239000005720 sucrose Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- 229920001897 terpolymer Polymers 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 239000004408 titanium dioxide Substances 0.000 description 2
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 1
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 description 1
- LVKKFNORSNCNPP-UHFFFAOYSA-N 2,2-bis(prop-2-enoylamino)acetic acid Chemical compound C=CC(=O)NC(C(=O)O)NC(=O)C=C LVKKFNORSNCNPP-UHFFFAOYSA-N 0.000 description 1
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 1
- OLPZCIDHOZATMA-UHFFFAOYSA-N 2,2-dioxooxathiiran-3-one Chemical class O=C1OS1(=O)=O OLPZCIDHOZATMA-UHFFFAOYSA-N 0.000 description 1
- RLYCRLGLCUXUPO-UHFFFAOYSA-N 2,6-diaminotoluene Chemical compound CC1=C(N)C=CC=C1N RLYCRLGLCUXUPO-UHFFFAOYSA-N 0.000 description 1
- NDWDBJJUEAHSHF-UHFFFAOYSA-N 2,6-dihydroxy-3,5-bis[4-(2-hydroxyethoxy)phenyl]-2,6-dimethylheptan-4-one Chemical compound C=1C=C(OCCO)C=CC=1C(C(C)(O)C)C(=O)C(C(C)(C)O)C1=CC=C(OCCO)C=C1 NDWDBJJUEAHSHF-UHFFFAOYSA-N 0.000 description 1
- PRAMZQXXPOLCIY-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)ethanesulfonic acid Chemical compound CC(=C)C(=O)OCCS(O)(=O)=O PRAMZQXXPOLCIY-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 description 1
- NXBXJOWBDCQIHF-UHFFFAOYSA-N 2-[hydroxy-[2-(2-methylprop-2-enoyloxy)ethoxy]phosphoryl]oxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOP(O)(=O)OCCOC(=O)C(C)=C NXBXJOWBDCQIHF-UHFFFAOYSA-N 0.000 description 1
- XEEYSDHEOQHCDA-UHFFFAOYSA-N 2-methylprop-2-ene-1-sulfonic acid Chemical compound CC(=C)CS(O)(=O)=O XEEYSDHEOQHCDA-UHFFFAOYSA-N 0.000 description 1
- UDXXYUDJOHIIDZ-UHFFFAOYSA-N 2-phosphonooxyethyl prop-2-enoate Chemical compound OP(O)(=O)OCCOC(=O)C=C UDXXYUDJOHIIDZ-UHFFFAOYSA-N 0.000 description 1
- PSLRXNFNXYNXEK-UHFFFAOYSA-N 2-triethoxysilylethyl prop-2-enoate Chemical compound CCO[Si](OCC)(OCC)CCOC(=O)C=C PSLRXNFNXYNXEK-UHFFFAOYSA-N 0.000 description 1
- KFNGWPXYNSJXOP-UHFFFAOYSA-N 3-(2-methylprop-2-enoyloxy)propane-1-sulfonic acid Chemical compound CC(=C)C(=O)OCCCS(O)(=O)=O KFNGWPXYNSJXOP-UHFFFAOYSA-N 0.000 description 1
- OIETYYKGJGVJFT-UHFFFAOYSA-N 3-[dimethyl-[3-(2-methylprop-2-enoylamino)propyl]azaniumyl]propane-1-sulfonate Chemical compound CC(=C)C(=O)NCCC[N+](C)(C)CCCS([O-])(=O)=O OIETYYKGJGVJFT-UHFFFAOYSA-N 0.000 description 1
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- MXRGSJAOLKBZLU-UHFFFAOYSA-N 3-ethenylazepan-2-one Chemical compound C=CC1CCCCNC1=O MXRGSJAOLKBZLU-UHFFFAOYSA-N 0.000 description 1
- URDOJQUSEUXVRP-UHFFFAOYSA-N 3-triethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CCO[Si](OCC)(OCC)CCCOC(=O)C(C)=C URDOJQUSEUXVRP-UHFFFAOYSA-N 0.000 description 1
- XDQWJFXZTAWJST-UHFFFAOYSA-N 3-triethoxysilylpropyl prop-2-enoate Chemical compound CCO[Si](OCC)(OCC)CCCOC(=O)C=C XDQWJFXZTAWJST-UHFFFAOYSA-N 0.000 description 1
- KBQVDAIIQCXKPI-UHFFFAOYSA-N 3-trimethoxysilylpropyl prop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C=C KBQVDAIIQCXKPI-UHFFFAOYSA-N 0.000 description 1
- MAGFQRLKWCCTQJ-UHFFFAOYSA-N 4-ethenylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(C=C)C=C1 MAGFQRLKWCCTQJ-UHFFFAOYSA-N 0.000 description 1
- IRQWEODKXLDORP-UHFFFAOYSA-N 4-ethenylbenzoic acid Chemical compound OC(=O)C1=CC=C(C=C)C=C1 IRQWEODKXLDORP-UHFFFAOYSA-N 0.000 description 1
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- 239000005711 Benzoic acid Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- HUPGJKIGPUTMBE-UHFFFAOYSA-N CCC[Y] Chemical compound CCC[Y] HUPGJKIGPUTMBE-UHFFFAOYSA-N 0.000 description 1
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- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 206010073306 Exposure to radiation Diseases 0.000 description 1
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- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
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- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- ZNXDCSVNCSSUNB-UHFFFAOYSA-N trimethoxy-[2-(oxiran-2-ylmethoxy)ethyl]silane Chemical compound CO[Si](OC)(OC)CCOCC1CO1 ZNXDCSVNCSSUNB-UHFFFAOYSA-N 0.000 description 1
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- VNTPGSZQKARKHG-UHFFFAOYSA-N trimethyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound C[Si](C)(C)CCCOCC1CO1 VNTPGSZQKARKHG-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M1/00—Inking and printing with a printer's forme
- B41M1/26—Printing on other surfaces than ordinary paper
- B41M1/34—Printing on other surfaces than ordinary paper on glass or ceramic surfaces
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M7/00—After-treatment of prints, e.g. heating, irradiating, setting of the ink, protection of the printed stock
- B41M7/0027—After-treatment of prints, e.g. heating, irradiating, setting of the ink, protection of the printed stock using protective coatings or layers by lamination or by fusion of the coatings or layers
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M7/00—After-treatment of prints, e.g. heating, irradiating, setting of the ink, protection of the printed stock
- B41M7/009—After-treatment of prints, e.g. heating, irradiating, setting of the ink, protection of the printed stock using thermal means, e.g. infrared radiation, heat
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B44—DECORATIVE ARTS
- B44C—PRODUCING DECORATIVE EFFECTS; MOSAICS; TARSIA WORK; PAPERHANGING
- B44C1/00—Processes, not specifically provided for elsewhere, for producing decorative surface effects
- B44C1/16—Processes, not specifically provided for elsewhere, for producing decorative surface effects for applying transfer pictures or the like
- B44C1/165—Processes, not specifically provided for elsewhere, for producing decorative surface effects for applying transfer pictures or the like for decalcomanias; sheet material therefor
- B44C1/17—Dry transfer
- B44C1/1712—Decalcomanias applied under heat and pressure, e.g. provided with a heat activable adhesive
- B44C1/1729—Hot stamping techniques
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/10—Printing inks based on artificial resins
- C09D11/101—Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M1/00—Inking and printing with a printer's forme
- B41M1/12—Stencil printing; Silk-screen printing
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M7/00—After-treatment of prints, e.g. heating, irradiating, setting of the ink, protection of the printed stock
- B41M7/0081—After-treatment of prints, e.g. heating, irradiating, setting of the ink, protection of the printed stock using electromagnetic radiation or waves, e.g. ultraviolet radiation, electron beams
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03H—HOLOGRAPHIC PROCESSES OR APPARATUS
- G03H1/00—Holographic processes or apparatus using light, infrared or ultraviolet waves for obtaining holograms or for obtaining an image from them; Details peculiar thereto
- G03H1/04—Processes or apparatus for producing holograms
- G03H1/18—Particular processing of hologram record carriers, e.g. for obtaining blazed holograms
- G03H2001/187—Trimming process, i.e. macroscopically patterning the hologram
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03H—HOLOGRAPHIC PROCESSES OR APPARATUS
- G03H2250/00—Laminate comprising a hologram layer
- G03H2250/10—Laminate comprising a hologram layer arranged to be transferred onto a carrier body
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03H—HOLOGRAPHIC PROCESSES OR APPARATUS
- G03H2250/00—Laminate comprising a hologram layer
- G03H2250/40—Printed information overlapped with the hologram
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/914—Transfer or decalcomania
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/24—Structurally defined web or sheet [e.g., overall dimension, etc.]
- Y10T428/24802—Discontinuous or differential coating, impregnation or bond [e.g., artwork, printing, retouched photograph, etc.]
- Y10T428/24851—Intermediate layer is discontinuous or differential
- Y10T428/24868—Translucent outer layer
- Y10T428/24876—Intermediate layer contains particulate material [e.g., pigment, etc.]
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/24—Structurally defined web or sheet [e.g., overall dimension, etc.]
- Y10T428/24802—Discontinuous or differential coating, impregnation or bond [e.g., artwork, printing, retouched photograph, etc.]
- Y10T428/24926—Discontinuous or differential coating, impregnation or bond [e.g., artwork, printing, retouched photograph, etc.] including ceramic, glass, porcelain or quartz layer
Landscapes
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Toxicology (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- General Health & Medical Sciences (AREA)
- Ceramic Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Thermal Sciences (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Surface Treatment Of Glass (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
- Details Of Rigid Or Semi-Rigid Containers (AREA)
Abstract
Description
grams | w/w % | ||
Vinyl caprolactam1 | 35.0 | 32.20 | ||
CAB 531-12 | 10.0 | 9.20 | ||
Tetrahydrofurfuryl acrylate3 | 20.0 | 18.40 | ||
Beta-carboxylethylacrylate4 | 15.0 | 13.80 | ||
Black pearl pigment | 10.0 | 9.20 | ||
Irgacure 18005 | 3.0 | 2.80 | ||
Irgacure 9076 | 3.0 | 2.80 | ||
Foamex N7 | 1.5 | 1.40 | ||
A-13108 | 0.5 | 0.50 | ||
3-methacryloxypropyl trimethoxysilane9 | 0.5 | 0.50 | ||
Epoxy acrylate + tripropylene glycol acrylate10 | 5.0 | 4.60 | ||
SB500E5011 | 5.0 | 4.60 | ||
1V-Cap/RC, CAS Reg. No 2235-00-9, International Specialty Products, Wayne, New Jersey | ||||
2Cellulose acetate butyrate, CAS Reg. No. 009004-36-8, Eastman Chemical Company, Kingsport, TN | ||||
3SR285, Sartomer Company Inc. | ||||
4B-CEA, UCB Radcure Inc. | ||||
5A 50:50 blend of bis(2,6-dimethyoxybenzoyl)(2,4,4-trimethylpentyl)phospine oxide and 1-hydroxycyclohexyl phenyl ketone, Ciba-Geigy Corp. | ||||
62-methyl-1-[4-(methylthio)phenyl]-2-morpholino propan-1-one | ||||
7Polydimethylsiloxane dispersed in silicic acid, Goldschmidt Corporation, Hopewell, VA. | ||||
8Gamma-isocyanotopropyltriethoxysilane A-1310, Osi Specialities, Inc. | ||||
9DYNASYLAN MEMO, Huls America Inc. (Sivento) | ||||
10CN104, Sartomer Company | ||||
11Aromatic acid methacrylate ½ ester in ethoxylated trimethylolpropane triacrylate, Sartomer Company |
Claims (20)
Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US09/134,825 US6562172B1 (en) | 1998-08-17 | 1998-08-17 | Glass decorating method using ink compositions containing N-vinyl lactams |
AU55646/99A AU5564699A (en) | 1998-08-17 | 1999-08-16 | Glass decorating method using ink compositions containing n-vinyl lactams |
JP2000564812A JP2002522341A (en) | 1998-08-17 | 1999-08-16 | Glass decoration method using N-vinyllactam-containing ink composition |
IL14147799A IL141477A0 (en) | 1998-08-17 | 1999-08-16 | Glass decorating method using ink compositions containing n-vinyl lactams |
EP99942217A EP1121246A1 (en) | 1998-08-17 | 1999-08-16 | Glass decorating method using ink compositions containing n-vinyl lactams |
CA002340918A CA2340918A1 (en) | 1998-08-17 | 1999-08-16 | Glass decorating method using ink compositions containing n-vinyl lactams |
PCT/US1999/018598 WO2000009332A1 (en) | 1998-08-17 | 1999-08-16 | Glass decorating method using ink compositions containing n-vinyl lactams |
BR9913468-3A BR9913468A (en) | 1998-08-17 | 1999-08-16 | Process for decorating a glassy substrate |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US09/134,825 US6562172B1 (en) | 1998-08-17 | 1998-08-17 | Glass decorating method using ink compositions containing N-vinyl lactams |
Publications (1)
Publication Number | Publication Date |
---|---|
US6562172B1 true US6562172B1 (en) | 2003-05-13 |
Family
ID=22465191
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US09/134,825 Expired - Fee Related US6562172B1 (en) | 1998-08-17 | 1998-08-17 | Glass decorating method using ink compositions containing N-vinyl lactams |
Country Status (8)
Country | Link |
---|---|
US (1) | US6562172B1 (en) |
EP (1) | EP1121246A1 (en) |
JP (1) | JP2002522341A (en) |
AU (1) | AU5564699A (en) |
BR (1) | BR9913468A (en) |
CA (1) | CA2340918A1 (en) |
IL (1) | IL141477A0 (en) |
WO (1) | WO2000009332A1 (en) |
Cited By (16)
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US20020114601A1 (en) * | 2000-11-30 | 2002-08-22 | Manabu Kagami | Method for manufacturing optical transmission device |
US20050025891A1 (en) * | 2003-07-25 | 2005-02-03 | Tang Robert H. | Method and compositions for coating ceramic substrates |
US20050028895A1 (en) * | 2001-09-05 | 2005-02-10 | Frank Walter | Radiation curable precious metal preparation, transfers containing same and method for decoration |
US20050069714A1 (en) * | 2003-09-30 | 2005-03-31 | Hart Terence J. | Method and compositions for improving durability of coated or decorated ceramic substrates |
US20070154632A1 (en) * | 2006-01-05 | 2007-07-05 | Wolfgang Schaefer | UV-curing glass printing ink and UV-curing glass printing lacquer and process for printing glass substrates |
US20070213427A1 (en) * | 2003-10-21 | 2007-09-13 | Saskia Lehmann | Uv Hardening Glass Printing Ink And Uv Hardening Glass Printing Lacquer And Method For Printing A Glass Substrate |
US20100028701A1 (en) * | 2006-10-30 | 2010-02-04 | Sika Technology Ag | Free-radically curable composition comprising polymerizable monomer and free-radical initiator |
US20110008547A1 (en) * | 2008-03-26 | 2011-01-13 | Sun Chemical, B.V. | jet ink and ink jet printing process |
US20110082105A1 (en) * | 2009-10-07 | 2011-04-07 | Fevola Michael J | Compositions comprising superhydrophilic amphiphilic copolymers and methods of use thereof |
US20110081309A1 (en) * | 2009-10-07 | 2011-04-07 | Fevola Michael J | Compositions comprising a superhydrophilic amphiphilic copolymer and a micellar thickener |
US20110082290A1 (en) * | 2009-10-07 | 2011-04-07 | Akzo Nobel Chemicals International B.V. | Superhydrophilic amphiphilic copolymers and processes for making the same |
US20110143047A1 (en) * | 2008-06-12 | 2011-06-16 | Durst Phototechnik Digital Technology Gmbh | Adhesion-promoting additive for an ink for imprinting glass |
US20120002138A1 (en) * | 2010-07-05 | 2012-01-05 | Chi-Mei Corporation | Pattern forming ink composition, light guide plate, light emitting unit and liquid crystal display element having the light emitting unit |
JP2015199856A (en) * | 2014-04-09 | 2015-11-12 | Dicグラフィックス株式会社 | active energy ray-curable offset ink composition |
US9689194B2 (en) | 2010-04-16 | 2017-06-27 | Saint-Gobain Glass France | Process and device for manufacturing a glazing unit comprising a decorative film, and glazing unit comprising a decorative film |
US11590749B2 (en) * | 2018-01-19 | 2023-02-28 | Hewlett-Packard Development Company, L.P. | Flexible packaging material |
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US6413618B1 (en) | 1999-05-11 | 2002-07-02 | Congoleum Corporation | Laminated glass floor tile and flooring made therefrom and method for making same |
JP3893262B2 (en) * | 2000-09-14 | 2007-03-14 | キヤノン株式会社 | Water-based photocurable resin composition, water-based ink, ink cartridge, recording unit, and ink jet recording apparatus |
JP5236171B2 (en) * | 2006-02-27 | 2013-07-17 | 富士フイルム株式会社 | INK COMPOSITION, INKJET RECORDING METHOD, PRINTED MATERIAL, AND METHOD FOR PRODUCING A lithographic printing plate |
JP5276264B2 (en) * | 2006-07-03 | 2013-08-28 | 富士フイルム株式会社 | INK COMPOSITION, INKJET RECORDING METHOD, PRINTED MATERIAL, AND METHOD FOR PRODUCING A lithographic printing plate |
JP5258237B2 (en) | 2006-09-14 | 2013-08-07 | 富士フイルム株式会社 | Ink composition, inkjet recording method, lithographic printing plate production method, and lithographic printing plate |
JP5159097B2 (en) * | 2006-09-22 | 2013-03-06 | 富士フイルム株式会社 | Ink composition, ink jet recording method and printed matter |
WO2009101401A1 (en) * | 2008-02-11 | 2009-08-20 | Sun Chemical B.V. | Inkjet inks and printing |
JP5572026B2 (en) | 2009-09-18 | 2014-08-13 | 富士フイルム株式会社 | Ink composition and inkjet recording method |
CN102701602B (en) * | 2012-06-12 | 2014-08-06 | 常州大学 | Method for initiating graft polymer through ultraviolet induction on surface of glass |
CZ2015299A3 (en) * | 2015-04-29 | 2016-04-06 | Heinz Glas Decor S.R.O. | Method of relief decoration of objects from rough or processed glass |
JP6606393B2 (en) * | 2015-09-30 | 2019-11-13 | 大日本塗料株式会社 | Active energy ray-curable ink composition for decorating inorganic substrates |
TW201842088A (en) * | 2017-02-08 | 2018-12-01 | 加拿大國家研究委員會 | Printable molecular ink |
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US5487927A (en) | 1992-01-24 | 1996-01-30 | Revlon Consumer Products Corporation | Decorating method and products |
US5585153A (en) | 1992-01-24 | 1996-12-17 | Revlon Consumer Products Corporation | Hot stamping glass |
US5656336A (en) | 1996-03-08 | 1997-08-12 | Revlon Consumer Products Corporation | Glass decorating method using bis-phenol-a epoxy resins and related compositions and articles |
US5665470A (en) * | 1994-07-27 | 1997-09-09 | National Starch And Chemical Investment Holding Corporation | Glass fibers and fiber-reinforced plastics |
US5750592A (en) * | 1992-08-04 | 1998-05-12 | Seiko Epson Corporation | Ink composition for ink jet recording |
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1998
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-
1999
- 1999-08-16 WO PCT/US1999/018598 patent/WO2000009332A1/en not_active Application Discontinuation
- 1999-08-16 BR BR9913468-3A patent/BR9913468A/en not_active Application Discontinuation
- 1999-08-16 CA CA002340918A patent/CA2340918A1/en not_active Abandoned
- 1999-08-16 AU AU55646/99A patent/AU5564699A/en not_active Abandoned
- 1999-08-16 JP JP2000564812A patent/JP2002522341A/en active Pending
- 1999-08-16 EP EP99942217A patent/EP1121246A1/en not_active Withdrawn
- 1999-08-16 IL IL14147799A patent/IL141477A0/en unknown
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US5487927A (en) | 1992-01-24 | 1996-01-30 | Revlon Consumer Products Corporation | Decorating method and products |
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US5750592A (en) * | 1992-08-04 | 1998-05-12 | Seiko Epson Corporation | Ink composition for ink jet recording |
US5665470A (en) * | 1994-07-27 | 1997-09-09 | National Starch And Chemical Investment Holding Corporation | Glass fibers and fiber-reinforced plastics |
US5656336A (en) | 1996-03-08 | 1997-08-12 | Revlon Consumer Products Corporation | Glass decorating method using bis-phenol-a epoxy resins and related compositions and articles |
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Cited By (27)
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US20020114601A1 (en) * | 2000-11-30 | 2002-08-22 | Manabu Kagami | Method for manufacturing optical transmission device |
US20050028895A1 (en) * | 2001-09-05 | 2005-02-10 | Frank Walter | Radiation curable precious metal preparation, transfers containing same and method for decoration |
US20050025891A1 (en) * | 2003-07-25 | 2005-02-03 | Tang Robert H. | Method and compositions for coating ceramic substrates |
US20050069714A1 (en) * | 2003-09-30 | 2005-03-31 | Hart Terence J. | Method and compositions for improving durability of coated or decorated ceramic substrates |
US20070213427A1 (en) * | 2003-10-21 | 2007-09-13 | Saskia Lehmann | Uv Hardening Glass Printing Ink And Uv Hardening Glass Printing Lacquer And Method For Printing A Glass Substrate |
US8501876B2 (en) | 2003-10-21 | 2013-08-06 | Marabuwerke Gmbh & Co. Kg | Glass printing ink or lacquer of epoxy resin, other resin and photoinitiator |
US20070154632A1 (en) * | 2006-01-05 | 2007-07-05 | Wolfgang Schaefer | UV-curing glass printing ink and UV-curing glass printing lacquer and process for printing glass substrates |
US8835530B2 (en) * | 2006-01-05 | 2014-09-16 | Marabu GmbH & Co., KG | UV-curing glass printing ink and UV-curing glass printing lacquer and process for printing glass substrates |
US20100028701A1 (en) * | 2006-10-30 | 2010-02-04 | Sika Technology Ag | Free-radically curable composition comprising polymerizable monomer and free-radical initiator |
US9421807B2 (en) | 2008-03-26 | 2016-08-23 | Sun Chemical B.V. | Jet ink and ink jet printing process |
US10807398B2 (en) | 2008-03-26 | 2020-10-20 | Sun Chemical Corporation | Jet ink and ink jet printing process |
US20110008547A1 (en) * | 2008-03-26 | 2011-01-13 | Sun Chemical, B.V. | jet ink and ink jet printing process |
US9260615B2 (en) | 2008-06-12 | 2016-02-16 | Durst Phototechnik Digital Technology Gmbh | Adhesion-promoting additive for an ink for imprinting glass |
US20110143047A1 (en) * | 2008-06-12 | 2011-06-16 | Durst Phototechnik Digital Technology Gmbh | Adhesion-promoting additive for an ink for imprinting glass |
US9114154B2 (en) * | 2009-10-07 | 2015-08-25 | Johnson & Johnson Consumer Inc. | Compositions comprising superhydrophilic amphiphilic copolymers and methods of use thereof |
US8399590B2 (en) | 2009-10-07 | 2013-03-19 | Akzo Nobel Chemicals International B.V. | Superhydrophilic amphiphilic copolymers and processes for making the same |
US20120316099A1 (en) * | 2009-10-07 | 2012-12-13 | Fevola Michael J | Compositions comprising superhydrophilic amphiphilic copolymers and methods of use thereof |
US8258250B2 (en) * | 2009-10-07 | 2012-09-04 | Johnson & Johnson Consumer Companies, Inc. | Compositions comprising superhydrophilic amphiphilic copolymers and methods of use thereof |
US9243074B2 (en) | 2009-10-07 | 2016-01-26 | Akzo Nobel Chemicals International B.V. | Superhydrophilic amphiphilic copolymers and processes for making the same |
US20110082290A1 (en) * | 2009-10-07 | 2011-04-07 | Akzo Nobel Chemicals International B.V. | Superhydrophilic amphiphilic copolymers and processes for making the same |
US20110081309A1 (en) * | 2009-10-07 | 2011-04-07 | Fevola Michael J | Compositions comprising a superhydrophilic amphiphilic copolymer and a micellar thickener |
US20110082105A1 (en) * | 2009-10-07 | 2011-04-07 | Fevola Michael J | Compositions comprising superhydrophilic amphiphilic copolymers and methods of use thereof |
US11173106B2 (en) | 2009-10-07 | 2021-11-16 | Johnson & Johnson Consumer Inc. | Compositions comprising a superhydrophilic amphiphilic copolymer and a micellar thickener |
US9689194B2 (en) | 2010-04-16 | 2017-06-27 | Saint-Gobain Glass France | Process and device for manufacturing a glazing unit comprising a decorative film, and glazing unit comprising a decorative film |
US20120002138A1 (en) * | 2010-07-05 | 2012-01-05 | Chi-Mei Corporation | Pattern forming ink composition, light guide plate, light emitting unit and liquid crystal display element having the light emitting unit |
JP2015199856A (en) * | 2014-04-09 | 2015-11-12 | Dicグラフィックス株式会社 | active energy ray-curable offset ink composition |
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Also Published As
Publication number | Publication date |
---|---|
EP1121246A1 (en) | 2001-08-08 |
JP2002522341A (en) | 2002-07-23 |
WO2000009332A1 (en) | 2000-02-24 |
IL141477A0 (en) | 2002-03-10 |
AU5564699A (en) | 2000-03-06 |
CA2340918A1 (en) | 2000-02-24 |
BR9913468A (en) | 2001-06-05 |
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